CHAPTER 2

Carbon Compounds

2.1 Carbon Compounds

Carbon compounds:
Compounds that contain carbon as one of
their constituent elements

Carbon compounds
Organic compounds
Carbon-containing
compounds that can
be obtained from
living things
Except oxides of
carbon, carbonates,
cyanides and metallic
carbides
Examples:

Inorganic compounds
Non-carbon-containing

compounds that can be

obtained from non-living
things
Include oxides of carbon,
carbonates, cyanides and
metallic carbides
Examples:

Hydrocarbon
Hydrocarbon:
Organic compounds which contains carbon and
hydrogen only
Examples:
Petroleum, coal, natural gas, rubber tree
Non-hydrocarbon:
Organic compounds containing carbon, hydrogen
together with a few other elements
Examples:
Sugar

Organic compounds
Hydrocarbons

Non-hydrocarbons

C and H

C, H and O, N, P, S, F,
Cl, Br and I

Saturated
hydrocarbon
Contain only

single bonds

Unsaturated
hydrocarbon
Contain at least

one multiple
bonds

Combustion products of organic compounds

When an organic compound burnt in excess
oxygen, the main product are carbon dioxide,
CO2 and water, H2O
C6H12O6 + 6O2 6CO2 + 6H2O
glucose

Alkanes, alkenes, alcohols,

carboxylic acids and esters

1. Molecular formula
Meaning
The formula that shows the actual numbers
and types of atoms present in a molecule.
Molecular formula
Explanation
Propane, C3H8
Contains 3 carbon atoms and 8
hydrogen atoms
Pentane, C5H12

Contains 5 carbon atoms and 12

hydrogen atoms

2. Structural formula
Meaning
The formula that shows how the atoms in a
molecule are bonded together and by what
types of bonds
Molecular formula
Propane, C3H8

Structural formula

3. Naming of carbon compound (IUPAC)

Guideline to naming the carbon compound:
Have 2 components
Show the number
of carbon atoms in
the molecules

Root

Show the family

of the compound

Ending

a) stem/root
Number of
carbon
atom

10

Stem

Meth

Eth

Prop

But

Pent

Hex

Hept

Oct

Non

Dec

b) suffix/ending
Ending; different followed by the
homologous series
Homologous series

Ending

Alkane

ane

Alkene

ene

Alcohol

ol

Carboxylic acid

oic acid

Ester

yl ..oate

B. ALKANES
Physical properties of alkanes
Alkanes are covalent compounds which
consist of simple molecules
Molecules are held together by weak
intermolecular force

Solubility

Density

Dissolve in
organic solvents
Insoluble in
water

Less dense than

water

Low melting &

boiling point

Electrical
conductivity
Cannot conduct
electricity
Because there
are no free
moving ions

Melting and
boiling point

Physical
properties of
alkanes

Physical state at
room
temperature
C1 to C4 are gases
C5 to C17 are
liquid
C18 > are solid

Explain the effect of the increase in number of

carbon atoms in alkane molecules

Size of molecule increase

Melting point & boiling point increase
The higher the number of carbon atoms, the
higher the melting & boiling point

 As the number of carbon atoms increases, the

molecule become bigger
The force of attraction between the molecules
become stronger
More heat energy is needed to overcome the
strong force of attraction between molecules

Why melting and boiling point propane is higher

than ethane?
Propane have more number of carbon atoms per
molecule than ethane
Size of propane is bigger than ethane
The force of attraction between propane
molecule increase
More heat energy is needed to overcome the
force of attraction between propane molecule
So, melting and boiling point of propane is higher
than ethane

Chemical properties of alkanes

Combustion
a) Complete combustion: produce CO2 + H2O
C2H6 + O2 CO2 + H2O
b) Incomplete combustion: produce CO/C gas +
H2O
2CH4 + 3O2 2CO + 4H2O
CH4 + O2 C + 2H2O

Halogenation
Reactions of alkanes with halogens
Take place readily in sunlight/ultraviolet
Example of substitution reaction
Reaction that occurs when one
atom or a group of atoms in a
molecule is replaced by another
atom or group of atoms

 CH4 + Cl2 CH3Cl + HCl

CH3Cl + Cl2
CH2Cl2 + Cl2

CHCl3 + Cl2

C. ALKENES
Physical properties of alkenes are similar to
alkanes
Molecules are held together by weak
intermolecular force

Solubility

Density
Less dense than
water

Dissolve in organic
solvents
Insoluble in water

Electrical
conductivity
Cannot conduct
electricity
Because there are
no free moving
ions

Melting and
boiling point
Physical
properties of
alkenes

Low melting &

boiling point

Explain the effect of the increase in number of

carbon atoms in alkene molecules

Size of molecule increase

Melting point & boiling point increase
The higher the number of carbon atoms, the
higher the melting & boiling point

Why melting and boiling point butene is higher

than ethene?
Butene have more number of carbon atoms per
molecule than ethene
Size of butene is bigger than ethene
The force of attraction between butene molecule
increase
More heat energy is needed to overcome the
force of attraction between butene molecule
So, melting and boiling point of butene is higher
than ethene

Chemical properties of alkenes

Combustion
(a) Complete combustion: produce CO2 + H2O
C2H4 + O2 CO2 + 2H2O
(a) Incomplete combustion:
produce CO/C gas + H2O
C2H4 + 2O2 2CO + 2H2O
C2H4 + O2 2C + 2H2O

Hydrogenation
Alkenes react with hydrogen at 180 C at
presence of nickel/platinum (catalyst) to
produce alkanes
C2H4 + H2

Ni, 180 C

C2H6

Halogenation
No catalyst or ultraviolet is needed
Alkenes react with halogen at room
temperature in the presence of
tetrachloromethane, CCl4
C2H4 + Cl2 C2H4Cl2
C4H8 + Br2 C4H8Br2
Used to test for the presence of a carbon-carbon double bond

Hydration
Alkenes reacts with steam, H2O at 300 C and
60 atm in the presence of concentrated H3PO4
(as catalyst) to produce alcohol
C2H4 + H2O

H3PO4
300 C, 60 atm

C2H5OH

Addition of hydrogen halides HX

Hydrogen halides: Hydrogen chloride, HCl or
hydrogen bromide, HBr
Alkenes reacts with hydrogen halide, HX at
room temperature to produce haloalkane
C2H4 + HCl C2H5Cl

Addition of hydroxyl group

Alkenes react with acidified potassium
manganate(VII), KMnO4 to produce diol
compound
C2H4 + H2O + [O] C2H4(OH)2
or
C2H4

KMnO4

C2H4(OH)2

Used to test for the presence of a carbon-carbon double bond

Polymerization reaction
Small alkene molecules undergo an addition
reaction with one another at high pressure of
1000 atm and temperature 200 C

Compare & contrast alkanes with alkenes

What do alkanes and alkenes have in
common?
How do they differ from each other?

Comparing chemical properties

Reactivity
Procedure:
1. Pour 2 cm3 of propane and propene into each
crucible.
2. The liquids are lighted.
3. When burning occurs, filter paper is placed
on top of the flame.
4. All the observation is recorded.

Observation:
Propane:
Burn in air, producing yellow sooty flame
Propene:
Burn in air, producing yellow and a very sooty flame
Conclusion:
Propene is more reactive than propane

Describe two chemical test to differentiate

between hexane and hexene

 Reaction with bromine water

Procedure:
1. Pour about [2-5 ] of hexane into a test tube.
2. Add 4-5 drops of bromine water and shake it.
3. Observe any changes and repeat with hexene.
Observation:
Hexane: Brown colour of bromine remains unchanged
Hexene: Brown colour of bromine decolourise/turn
colourless

 Reaction with acidified potassium manganate(VII) solution

Procedure:
1. Pour about [2-5 ] of hexane into a test tube.
2. Add 4-5 drops of acidified potassium manganate(VII)
solution and shake it.
3. Observe any changes and repeat with hexene.
Observation:
Hexane: Purple colour of KMnO4 remains unchanged
Hexene: Purple colour of KMnO4 decolourise/turn colourless

Determine which one is more soot between

hexane and hexene when burn in oxygen. Give
your reason.

Hexane, C6H14
=
6(12)
x 100
[6(12)+14(1)]
= 83.72%

Hexene, C6H12
=
6(12)
x 100
[6(12)+12(1)]
= 85.71%

Hexene has high percentage of carbon by mass than

hexane.
So, hexene burn with more sooty flame

Solubility
Slightly soluble in
water but readily
dissolve in organic
solvent

State
Simple ester is
colourless liquid at
room condition

Density
Low density

Boiling point
Low boiling
point

Odour
Physical
properties of
ester

Sweet pleasant
smell (fruity
smell)

E. ALCOHOL
Industrial production of ethanol
Two main process:
(a)From sugar and starch by fermentation
(b)From petroleum fraction by hydration

1. Fermentation
C6H12O6 2C2H5OH + 2CO2
From sugar & starches
Yeast added
Left in warm place (absence of oxygen)anaerobic
Temperature = 18 20 C
Catalyst = yeast (zymase)
Other condition = absence of oxygen

2. Hydration
CH + H2O C2H5OH
From petroleum fractions
Temperature = 300 C
Pressure = 60 atm
Catalyst = phosporic acid, H3PO4

Chemical properties of alcohols

Combustion
(a) Complete combustion: produce CO2 + H2O

C2H5OH + 3O2 2CO2 + 3H2O

Oxidation reaction
React with the oxidation agent:
a) acidified potassium manganate(VII), KMnO4
(purple colourless)
b) acidified potassium dichromate(VI), K2Cr2O7
(orange green)
C2H5OH+ 2[O] CH3COOH + H2O
Ethanol

Ethanoic acid

Dehydration
Removal of water molecule from alcohol
molecule
C2H5OH C2H4 + H2O
Ethanol

Ethene

Method:
(a) Heated under reflux at 180 C with excess
concentrated H2SO4 or
(b) Pass over a heated catalyst (porcelain chips,
porous pot, Al2O3

Uses of alcohols
As a solvent in
Perfumes, cosmetics, toiletries
As a thinner in
Lacquer, varnish, shellac, ink
As a cleaner for
Compact disc, video cassette recorder head
As a fuel
Clean fuel, biofuel, gasohol

As a raw material in manufacture of

Vinegar, fibre, explosive, plastic
As a raw material to make pharmaceutical
products
Tincture, antiseptic, cough syrup, rubbing
alcohol

F. CARBOXYLIC ACIDS
Functional group
Carboxyl group ( -COOH )
General formula
CnH2n+1COOH

Solubility
Simple molecules are
very soluble in water
Due to water molecule
being strongly
attracted to the
COOH group
Solubility when
number of carbon per
molecule

State
Larger molecules
(C10 above) are
wax-like solids

Colour
Colourless
liquid

Boiling point
High boiling
point

Physical
properties of
carboxylic
acids

Odour
Sharp/unplea
sant smell

Synthesised/making of ethanoic acids

Oxidation of alcohol
C2H5OH+ 2[O] CH3COOH + H2O
Ethanol

Ethanoic acid

Reflux ethanol with acidified potassium

dichromate(VI) solution or acidified potassium
manganate(VII) solution

Chemical properties
Acid properties
CH3COOH is a weak monoprotic acid
Only one hydrogen atom can ionize in water to
produce H+ ion
CH3COOH CH3COO- + H+
Ethanoic acid

Ethanoate ion

Partially dissociate in water

Turn moist blue litmus red
React slowly with metals, bases and carbonates

Reaction with metals

Carboxylic acid + metal salt + H2
2CH3COOH + Zn Zn(CH3COO)2 + H2
Ethanoic acid

Zinc ethanoate

Reaction with bases

Carboxylic acid + bases salt + H2O
CH3COOH + NaOH CH3COONa + H2O
Ethanoic acid

Sodium
ethanoate

2CH3COOH + CuO Cu(CH3COO) 2 + H2O

Ethanoic acid

Copper
ethanoate

Reaction with carbonates

Carboxylic acid + carbonates salt + CO2 + H2O
2CH3COOH + CaCO3 Ca(CH3COO)2 + CO2 + H2O
Ethanoic acid

Calcium
ethanoate

Reaction with alcohols

Carboxylic acid + alcohol ester + H2O
Catalyst: Concentrated H2SO4
CH3COOH + C4H9OH CH3COOC4H9 + H2O
Ethanoic
acid

Butan-1-ol

Buthyl ethanoate

Uses of carboxylic acids

Ethanoic acid
As a flavouring
As a preservative
Used with other chemicals to make drugs, dyes, paints,
insecticides and plastics
Methanoic acid
Used to coagulate latex
Fatty acids (long-chain carboxylic acids)
Used in making soaps
Benzoic acid
Preservative in food

G. ESTER
Functional group
Carboxylate group ( -COO- )

General formula
CnH2n+1COOCmH2m+1
Naming ester

Boiling point

Colour
Solubility
Simple
alcohols are
very soluble
in water
Because has
OH group

Colourless
liquid at room
temperature

Low boiling
point
compare to
water

Odour
Very sharp
smell

State
C1 to C11 are
liquid at room
temperature

Physical
properties of
alcohol

Highly
volatile

Formation of ester
Esterification reaction
Catalyst: Concentrated H2SO4

Natural sources
Fruit
Pineapple C3H7COOC2H5
Ethyl butanoate
Flower
Jasmine CH3COOCH2C6H5
Benzyl ethanoate

Use of ester
Preparation of cosmetics & perfumes
Used as food additives (enhance the flavour &
smell of processed food)
Production of soap & detergent